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The 228 Best Holiday Party Entertainers for Hire in Chelsea, MA

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269 Holiday Party Entertainers serving Chelsea, MA
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Matt Roberts: Clean Comedy Magic - Magician / Holiday Party Entertainment in Boston, Massachusetts Featured vendor banner

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Matt Roberts: Clean Comedy Magic - Magician / Holiday Party Entertainment in Boston, Massachusetts

Matt Roberts: Clean Comedy Magic

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5.0 (29)
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  • Map pin icon Boston, MA
  • Vendor category icon Magician / Holiday Party Entertainment
  • Travel distance icon 3 miles from Chelsea
  • Check mark icon 39 Verified Bookings

Rob A. said “Matt was booked for our Cub Scout Blue and Gold Banquet of approximately 100 people. The boys are between ages 5 and 10 and they are not the easiest people…”

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Gillian Berkowitz - Pianist / Holiday Party Entertainment in Boston, Massachusetts Featured vendor banner

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Gillian Berkowitz - Pianist / Holiday Party Entertainment in Boston, Massachusetts

Gillian Berkowitz

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5.0 (29)
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  • Map pin icon Boston, MA
  • Vendor category icon Pianist / Holiday Party Entertainment
  • Travel distance icon 3 miles from Chelsea
  • Check mark icon 30 Verified Bookings

Kraig K. said “Super responsive and very talented. Would highly recommend!”

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Mega Magic- Magician Mike D'Urzo - Magician / Holiday Party Entertainment in Boston, Massachusetts Featured vendor banner

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Mega Magic- Magician Mike D'Urzo - Magician / Holiday Party Entertainment in Boston, Massachusetts

Mega Magic- Magician Mike D'Urzo

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5 (11)
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  • Map pin icon Boston, MA
  • Vendor category icon Magician / Holiday Party Entertainment
  • Travel distance icon 3 miles from Chelsea
  • Check mark icon 6 Verified Bookings

Sam H. said “We hired Mike for a team building event. It was a smaller event with 30 people but Mike was amazing. We combined motivation and magic to kick off the…”

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The Creswell Club - Jazz Band / Holiday Party Entertainment in Boston, Massachusetts Featured vendor banner

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The Creswell Club - Jazz Band / Holiday Party Entertainment in Boston, Massachusetts

The Creswell Club

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5.0 (23)
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  • Map pin icon Boston, MA
  • Vendor category icon Jazz Band / Holiday Party Entertainment
  • Travel distance icon 3 miles from Chelsea
  • Check mark icon 23 Verified Bookings

Matthew C. said “Controlled the atmosphere set the mardi gras vibe”

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Gerry Beaudoin Trio - Jazz Band / Holiday Party Entertainment in Boston, Massachusetts Featured vendor banner
Gerry Beaudoin Trio - Jazz Band / Holiday Party Entertainment in Boston, Massachusetts

Gerry Beaudoin Trio

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5 (29)
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  • Map pin icon Boston, MA
  • Vendor category icon Jazz Band / Holiday Party Entertainment
  • Travel distance icon 3 miles from Chelsea
  • Check mark icon 46 Verified Bookings

Siobhan O. said “Great jazz trio easy to work with. Arrived ahead of schedule accommodating to crowd. Just perfect”

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The Donnino Mentalists - Beyond Imagination! - Magician / Holiday Party Entertainment in Brighton, Massachusetts Featured vendor banner

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The Donnino Mentalists - Beyond Imagination! - Magician / Holiday Party Entertainment in Brighton, Massachusetts

The Donnino Mentalists - Beyond Imagination!

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5.0 (12)
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  • Map pin icon Brighton, MA
  • Vendor category icon Magician / Holiday Party Entertainment
  • Travel distance icon 7 miles from Chelsea
  • Check mark icon 5 Verified Bookings

Ames T. said “Mike and the family performed for me and about 20 of my friends (all in our mid 20's) and they were FANTASTIC. They involved much of the audience, amazed…”

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Great Scott Productions - Magician / Holiday Party Entertainment in Rockland, Massachusetts Featured vendor banner

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Great Scott Productions - Magician / Holiday Party Entertainment in Rockland, Massachusetts

Great Scott Productions

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4.86 (45)
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  • Map pin icon Rockland, MA
  • Vendor category icon Magician / Holiday Party Entertainment
  • Travel distance icon 19 miles from Chelsea
  • Check mark icon 95 Verified Bookings

Nancy H. said “Scott did a great job putting on a magic show for our seniors at Lunch & Learn. They really enjoyed it.”

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Santa Dan - Santa Claus / Holiday Party Entertainment in Taunton, Massachusetts Featured vendor banner
Santa Dan - Santa Claus / Holiday Party Entertainment in Taunton, Massachusetts

Santa Dan

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5.0 (39)
Top Performer badge
  • Map pin icon Taunton, MA
  • Vendor category icon Santa Claus / Holiday Party Entertainment
  • Travel distance icon 34 miles from Chelsea
  • Check mark icon 78 Verified Bookings

Douglas L. said “Everyone ennjoed Santa’s visit! He spent alotof time passing out gifts and taking photos with everyone We will certainly have him back!”

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Holiday Victorian Carolers - Christmas Carolers / Holiday Party Entertainment in Boston, Massachusetts Featured vendor banner
Holiday Victorian Carolers - Christmas Carolers / Holiday Party Entertainment in Boston, Massachusetts

Holiday Victorian Carolers

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4.96 (22)
  • Map pin icon Boston, MA
  • Vendor category icon Christmas Carolers / Holiday Party Entertainment
  • Travel distance icon 3 miles from Chelsea
  • Check mark icon 34 Verified Bookings

Sean A. said “Perfect”

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Background Jazz Band - Jazz Band / Holiday Party Entertainment in Boston, Massachusetts Featured vendor banner
Background Jazz Band - Jazz Band / Holiday Party Entertainment in Boston, Massachusetts

Background Jazz Band

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4.85 (9)
  • Map pin icon Boston, MA
  • Vendor category icon Jazz Band / Holiday Party Entertainment
  • Travel distance icon 3 miles from Chelsea
  • Check mark icon 22 Verified Bookings

Elizabeth S. said “Perfect music for my cocktail party. So easy to coordinate with. Very professional and just all around great!”

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Awesome ROBB - Magician / Holiday Party Entertainment in Boston, Massachusetts Featured vendor banner
Awesome ROBB - Magician / Holiday Party Entertainment in Boston, Massachusetts

Awesome ROBB

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4.99 (21)
  • Map pin icon Boston, MA
  • Vendor category icon Magician / Holiday Party Entertainment
  • Travel distance icon 3 miles from Chelsea
  • Check mark icon 3 Verified Bookings

Laura B. said “We hired Robb for my son's birthday party (turning 3!) and he was spectactular - totally understood how to cater to the younger crowd without losing the…”

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Louis Pettinelli Entertainment - Jazz Band / Holiday Party Entertainment in Boston, Massachusetts Featured vendor banner

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Louis Pettinelli Entertainment - Jazz Band / Holiday Party Entertainment in Boston, Massachusetts

Louis Pettinelli Entertainment

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4.87 (47)
  • Map pin icon Boston, MA
  • Vendor category icon Jazz Band / Holiday Party Entertainment
  • Travel distance icon 3 miles from Chelsea
  • Check mark icon 136 Verified Bookings

Lisa C. said “As stated above. Band was on time from beginning to end, great singer and musicians. Played like they have been together a life time although they just…”

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The Ultimate Cocktail Party by Cheryl - Bartender / Holiday Party Entertainment in Boston, Massachusetts Featured vendor banner

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The Ultimate Cocktail Party by Cheryl - Bartender / Holiday Party Entertainment in Boston, Massachusetts

The Ultimate Cocktail Party by Cheryl

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5.0 (16)
  • Map pin icon Boston, MA
  • Vendor category icon Bartender / Holiday Party Entertainment
  • Travel distance icon 3 miles from Chelsea
  • Check mark icon 47 Verified Bookings

Nina S. said “Cheryl made our lives so much easier by helping at our son’s birthday. My husband and I were able to enjoy the event instead of worrying about food being…”

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The Gatsby Gang Jazz Band - Jazz Band / Holiday Party Entertainment in Boston, Massachusetts Featured vendor banner
The Gatsby Gang Jazz Band - Jazz Band / Holiday Party Entertainment in Boston, Massachusetts

The Gatsby Gang Jazz Band

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5.0 (3)
  • Map pin icon Boston, MA
  • Vendor category icon Jazz Band / Holiday Party Entertainment
  • Travel distance icon 3 miles from Chelsea
  • Check mark icon 9 Verified Bookings

Karin J. said “Couldn’t be happier with these musicians! If you are looking for a traditional jazz trio feel like we were, don’t look any further. This is your group!!…”

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Marvelous Santas - Santa Claus / Holiday Party Entertainment in Saugus, Massachusetts Featured vendor banner

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Marvelous Santas - Santa Claus / Holiday Party Entertainment in Saugus, Massachusetts

Marvelous Santas

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5.0 (11)
  • Map pin icon Saugus, MA
  • Vendor category icon Santa Claus / Holiday Party Entertainment
  • Travel distance icon 5 miles from Chelsea
  • Check mark icon 15 Verified Bookings

Chris D. said “Santa Brian was very helpful in preparation of our event as well as in his appearance. Santa read a scripted holiday 'nice and naughty' list that I put…”

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Eaden Marti: Magician & Mentalist - Magician / Holiday Party Entertainment in Dorchester, Massachusetts Featured vendor banner

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Eaden Marti: Magician & Mentalist - Magician / Holiday Party Entertainment in Dorchester, Massachusetts

Eaden Marti: Magician & Mentalist

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4.97 (32)
  • Map pin icon Dorchester, MA
  • Vendor category icon Magician / Holiday Party Entertainment
  • Travel distance icon 6 miles from Chelsea
  • Check mark icon 37 Verified Bookings

Deborah H. said “Eaden even managed to impress a room full of PhD scientists who tend to run on the very skeptical and cynical side. Folks left trying to figure how he…”

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Magic Fred - Magician / Holiday Party Entertainment in Lowell, Massachusetts Featured vendor banner

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Magic Fred - Magician / Holiday Party Entertainment in Lowell, Massachusetts

Magic Fred

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5.0 (27)
  • Map pin icon Lowell, MA
  • Vendor category icon Magician / Holiday Party Entertainment
  • Travel distance icon 22 miles from Chelsea
  • Check mark icon 23 Verified Bookings

Harika D. said “Completely blown away, not only by the amazing magic tricks, but by how creative, humorous, engaging, and just fun Magic Fred was for our virtual kids…”

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Jack Velour - Magician / Holiday Party Entertainment in Boston, Massachusetts Featured vendor banner
Jack Velour - Magician / Holiday Party Entertainment in Boston, Massachusetts

Jack Velour

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5.0 (15)
  • Map pin icon Boston, MA
  • Vendor category icon Magician / Holiday Party Entertainment
  • Travel distance icon 3 miles from Chelsea
  • Check mark icon 17 Verified Bookings

Colleen A. . C. N. I. I. said “Jack was amazing and helped make our corporate event a smash. Everyone was in Awww”

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Jazz Band for Holiday Parties - Jazz Band / Holiday Party Entertainment in Boston, Massachusetts Featured vendor banner
Jazz Band for Holiday Parties - Jazz Band / Holiday Party Entertainment in Boston, Massachusetts

Jazz Band for Holiday Parties

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0 (0)
  • Map pin icon Boston, MA
  • Vendor category icon Jazz Band / Holiday Party Entertainment
  • Travel distance icon 3 miles from Chelsea

We provide live jazz for Holiday and Christmas Parties!

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Munsey's Magic - Magician / Holiday Party Entertainment in Medford, Massachusetts Featured vendor banner

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Munsey's Magic - Magician / Holiday Party Entertainment in Medford, Massachusetts

Munsey's Magic

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5.0 (52)
  • Map pin icon Medford, MA
  • Vendor category icon Magician / Holiday Party Entertainment
  • Travel distance icon 4 miles from Chelsea

Anastasia B. said “Munsey's Magic is the real deal!! You will never find a better magician. I first witnessed Mr. Munsey's magical illusions in our geometry classroom in…”

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Mel Stiller - Pianist / Holiday Party Entertainment in Boston, Massachusetts
Mel Stiller - Pianist / Holiday Party Entertainment in Boston, Massachusetts

Mel Stiller

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5.0 (6)
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  • Map pin icon Boston, MA
  • Vendor category icon Pianist / Holiday Party Entertainment
  • Travel distance icon 3 miles from Chelsea
  • Check mark icon 7 Verified Bookings

Christa L. said “Mel is a blast to have for our dinner music once a month at our independent retirement community. He plays all the right music to get the group singing…”

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Fred Woodard - Jazz Band / Holiday Party Entertainment in Dorchester, Massachusetts
Fred Woodard - Jazz Band / Holiday Party Entertainment in Dorchester, Massachusetts

Fred Woodard

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5.0 (1)
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  • Map pin icon Dorchester, MA
  • Vendor category icon Jazz Band / Holiday Party Entertainment
  • Travel distance icon 6 miles from Chelsea
  • Check mark icon 2 Verified Bookings

Mike M. said “Fred and the guys were great. We received countless compliments on their performance. Would love to work with them again!”

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Wendee Glick & Friends - Jazz Band / Holiday Party Entertainment in Nashua, New Hampshire

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Wendee Glick & Friends - Jazz Band / Holiday Party Entertainment in Nashua, New Hampshire

Wendee Glick & Friends

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5.0 (11)
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  • Map pin icon Nashua, NH
  • Vendor category icon Jazz Band / Holiday Party Entertainment
  • Travel distance icon 34 miles from Chelsea
  • Check mark icon 16 Verified Bookings

Amy G. said “We hired Steve Heck and friends for my Dad's 90th Birthday celebration. It was a very small party due to Covid so I just needed a keyboard player/singer.…”

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Bela Sarkozy Trio - Jazz Band / Holiday Party Entertainment in Lakeville, Massachusetts
Bela Sarkozy Trio - Jazz Band / Holiday Party Entertainment in Lakeville, Massachusetts

Bela Sarkozy Trio

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4.9 (36)
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  • Map pin icon Lakeville, MA
  • Vendor category icon Jazz Band / Holiday Party Entertainment
  • Travel distance icon 38 miles from Chelsea
  • Check mark icon 23 Verified Bookings

Stephanie E. said “Bela and his group are a class act! Bela gathered a group of 3 jazz musicians short notice for our event. On top of being a fantastic musician, Bela was…”

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Cocktail Ladies - Bartender / Holiday Party Entertainment in Boston, Massachusetts
Cocktail Ladies - Bartender / Holiday Party Entertainment in Boston, Massachusetts

Cocktail Ladies

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5.0 (6)
  • Map pin icon Boston, MA
  • Vendor category icon Bartender / Holiday Party Entertainment
  • Travel distance icon 3 miles from Chelsea
  • Check mark icon 19 Verified Bookings

Sharon J. said “Cheryl, Kevin and Solo were such a great help to this big event at our home Saturday. We had over a 120 people attend. I was able to enjoy the party and…”

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Santa Don - Santa Claus / Holiday Party Entertainment in Halifax, Massachusetts
Santa Don - Santa Claus / Holiday Party Entertainment in Halifax, Massachusetts

Santa Don

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4.47 (17)
  • Map pin icon Halifax, MA
  • Vendor category icon Santa Claus / Holiday Party Entertainment
  • Travel distance icon 29 miles from Chelsea
  • Check mark icon 45 Verified Bookings

Karen B. said “We were so pleased with Santa Don. The children were so excited and loved his magical book. He made our party extra special. I would highly recommend…”

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Friendly Bartending - Bartender / Holiday Party Entertainment in Plainville, Massachusetts
Friendly Bartending - Bartender / Holiday Party Entertainment in Plainville, Massachusetts

Friendly Bartending

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0 (0)
  • Map pin icon Plainville, MA
  • Vendor category icon Bartender / Holiday Party Entertainment
  • Travel distance icon 31 miles from Chelsea
  • Check mark icon 2 Verified Bookings

Are you looking for a dependable bartender to take care of the most important part of any party? Then look no further. I am your guy. I have over 10 years of bartending…

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Seventh Sun - Jazz Band / Holiday Party Entertainment in Boston, Massachusetts
Seventh Sun - Jazz Band / Holiday Party Entertainment in Boston, Massachusetts

Seventh Sun

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0 (0)
  • Map pin icon Boston, MA
  • Vendor category icon Jazz Band / Holiday Party Entertainment
  • Travel distance icon 3 miles from Chelsea

Seventh Sun is a multi-genre ensemble that has worked and toured nationally performing with esteemed guests. Our ensemble is comprised of collegiate graduates from…

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The Jazz Committee - Jazz Band / Holiday Party Entertainment in Salem, New Hampshire
The Jazz Committee - Jazz Band / Holiday Party Entertainment in Salem, New Hampshire

The Jazz Committee

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5.0 (1)
  • Map pin icon Salem, NH
  • Vendor category icon Jazz Band / Holiday Party Entertainment
  • Travel distance icon 29 miles from Chelsea

Mark S. said “I hired Rick and his band to play for the cocktail hour for my daughter's wedding. Rick was a true professional from beginning to end. We discussed the…”

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Olde Towne Carolers Boston - Christmas Carolers / Holiday Party Entertainment in Boston, Massachusetts

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Olde Towne Carolers Boston - Christmas Carolers / Holiday Party Entertainment in Boston, Massachusetts

Olde Towne Carolers Boston

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5.0 (4)
  • Map pin icon Boston, MA
  • Vendor category icon Christmas Carolers / Holiday Party Entertainment
  • Travel distance icon 3 miles from Chelsea
  • Check mark icon 5 Verified Bookings

Lulu R. said “Lovely thank you!”

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Show More Holiday Party Entertainers Near You

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Quick facts
Holiday Party Entertainment in Chelsea, MA

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505th most popular

Holiday Party Entertainers rank #505 in popularity out of 545 categories on GigSalad

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Holiday Party Entertainment in Chelsea, MA


If you’re planning a holiday party this year, add even more festivities by booking the best live entertainment! Here are some tips to help you find the perfect professionals.

To start, make a list of the various styles of entertainment that you’re interested in. Jazz bands, classical ensembles, and Christmas carolers are popular options for background holiday music. For a corporate cocktail party, bartenders, waitstaff, and caterers offer everything you and your guests will need. Need something for the kiddos? Book a visit from Santa and Mrs. Claus and watch their faces light up! Once you’ve decided on your ideal holiday party entertainment, search online for professionals in your area. Most entertainers have online profiles so that you can get a feel for what they offer. Check out performance descriptions, listen to audio clips, and watch videos of their past events. If available, read through reviews from their past clients to gauge a performer’s experience and professionalism. When you’re ready to contact an entertainer for their rates and availability, make sure to give them as much information about your event as possible. Discuss important details such as performance space, power supply, scheduled breaks, parking, and any unique aspect of your event. The more info you give the vendor, the easier it is for them to provide a customized quote! Lastly, confirm the agreement and performance details in writing. With GigSalad, everything you need to find and book holiday party entertainment is in one simple platform. Browse profiles, get free quotes, and book with the added security of our Worry-Free Guarantee. Search for Holiday Party Entertainment in Chelsea, Massachusetts above.

Please note that these Holiday Party Entertainment may also travel to East Boston, Charlestown, Roxbury Crossing, New Town, West Medford, Allston, Brookline Village, Roxbury, Nahant, Dorchester, Jamaica Plain, Dorchester Center, Brighton, Waverley, Arlington Heights, Swampscott, Newton Corner, Chestnut Hill, Mattapan, Hull, Roslindale, Nonantum, Newton Center, Newtonville, North Waltham, Milton Village, Lynnfield, West Roxbury, West Newton, and Newton Highlands.

Find Holiday Party Entertainment in nearby cities

Revere Everett Boston Winthrop Malden Somerville
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